Spurs avoided their toughest draw, which would have been Ligue 1 giants Paris Saint-Germain, but the Serie A champions will still prove a stern test.
For Spurs manager Antonio Conte the tie, which will take place across two legs in February and March 202, is a return to Milan where he won the Scudetto with rivals Inter Milan just 18 months prior.
It is also a repeat of Tottenham’s first ever last-16 tie in the Champions League, coming back in the 2010-11 season in which Peter Crouch’s sole goal at San Siro earned a 1-0 aggregate win over two legs.
Milan will head into the fixture having already been beaten home and away by Chelsea in the group stage.
The last-16 first legs will take place across 14-15 and 21-22 February, with the second legs set to be played over 7-8 and 14-15 March.
Spurs will travel to Milan for the first leg before returning to the Tottenham Hotspur Stadium for the return fixture.